Ethanol → 6-(4-ethoxy-1H-quinazolin-2-ylidene)-1-cyclohexa-2,4-dienone

HRID 1798759Notes

Reaction equation

HRID 1798759 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[N:3]=1.ClCCl.[CH2:22]([OH:24])[CH3:23]>>[CH2:22]([O:24][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[OH:18])[N:3]=1)[CH3:23]

Participants

4

Reactant 3

HCID 702EthanolHCID 6344DichloromethaneHCID 40509562-(4-Chloroquinazolin-2-yl)phenol

Product 1

HCID 32441126-(4-ethoxy-1H-quinazolin-2-ylidene)-1-cyclohexa-2,4-dienone

Conditions

Temperature
180 °C

Procedure

2-(4-Chloro-quinazolin-2-yl)-phenol (50 mg, 0.196 mmol) was placed in a microwave tube charged with a stir bar and dissolved 0.5 ml dry dichloromethane, followed by the addition of 2 ml dry ethanol. Tube was sealed with a cap and heated at 160 to 200° C. for one hour in CEM microwave. Solvent was removed under reduced pressure, reconstituted organic in DMSO and purified by Gilson HPLC. The desired compound was concentrated to a white solid as the TFA salt. LC/MS (10-99%) M/Z 267.2, retention time 2.57 minutes.

Workup

  1. additioncharged with a stir bar
  2. customTube was sealed with
  3. customa cap
  4. customSolvent was removed under reduced pressure
  5. custompurified by Gilson HPLC
  6. concentrationThe desired compound was concentrated to a white solid as the TFA salt

Sources & evidence

ORD record
ord-28a66870cd3e4dbab5dfa11b1943cc3d
Source dataset
uspto-grants-2013_01
Patent number
US08343980B2

Reaction notes

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